Next Article in Journal
The Cyclic Nitronate Route to Pharmaceutical Molecules: Synthesis of GSK’s Potent PDE4 Inhibitor as a Case Study
Previous Article in Journal
Development and Validation of a TLC-Densitometry Method for Histamine Monitoring in Fish and Fishery Products
Previous Article in Special Issue
Computational Prediction of Chiral Iron Complexes for Asymmetric Transfer Hydrogenation of Pyruvic Acid to Lactic Acid
Open AccessArticle

A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes

1
International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
2
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Hans-Joachim Knölker
Molecules 2020, 25(16), 3612; https://doi.org/10.3390/molecules25163612
Received: 1 July 2020 / Revised: 3 August 2020 / Accepted: 5 August 2020 / Published: 8 August 2020
(This article belongs to the Special Issue Recent Advances in Iron Catalysis)
To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others. View Full-Text
Keywords: iron catalysis; haloalkane coupling; Grignard reagent; FeI/FeII/FeIII mechanism; density functional theory iron catalysis; haloalkane coupling; Grignard reagent; FeI/FeII/FeIII mechanism; density functional theory
Show Figures

Figure 1

MDPI and ACS Style

Sharma, A.K.; Nakamura, M. A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes. Molecules 2020, 25, 3612. https://doi.org/10.3390/molecules25163612

AMA Style

Sharma AK, Nakamura M. A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes. Molecules. 2020; 25(16):3612. https://doi.org/10.3390/molecules25163612

Chicago/Turabian Style

Sharma, Akhilesh K.; Nakamura, Masaharu. 2020. "A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes" Molecules 25, no. 16: 3612. https://doi.org/10.3390/molecules25163612

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop